Orange to red dyestuffs able to be chromated and a process of making same.



i; AGREE,

ll USTBY IN BASLE,

ORANGE T DYESTUFFS ABLE TO BE CHBOMATED AND A PROCESS 0F 01 BASEL, SWITZERLAND, ASSIGNOR T0 SOCIETY OF CHEMICAL 0F BASEL SWITZERLAND.

MAKING Patented Jan. 2, 11917.

SAME.

1 21@ 8@ Specification of Letters yatent. No Drawing.

- To all whom it may concern after they Be it known that I, Dr. CARL JAcERs- PAGHER, chemist, a citizen of the Swiss Republic, and resident of Basel, Switzerland, have invented new and useful Orange to Red Dyestuffs Able to be Chromated and a Process of Making Same, ofwhich the following is a full, clear, and exact specification.

It is known that only the diazo derivates of orthoaminonaphthols and of their substitution products give by their combination with the pyrazolones usually combined with azo bodies, dyestufls furnishing dyeings which are fast to fulling and to potting after they have been chromated, while the diazo derivates of orthoaminophenol and of its derivates do not give such dyestufis. Thus for instance the dyestufl orthodiazonaphtholsulfonic acid 1 :2 z H-phenylmethylpyrazolone is very fast to fulling and potting, phenolsulfonic acid phenylmethylpyrazolone possesses an absolutely insuficient fastness to fulling and potting.

I have now found, that it is possible to obtain, not only with the diazo derivates of orthoaminonaphthols and of their substitution products, but also with the diazo deriva-tes of orthoaminophenols and of their substitution products, azo dyestufis showing besides a very good fastness to fulling and potting also a prominent fastness to light, after they have been chromated, if the said diazoderivates are combined with the pyrazolones of the benzene and the naphthalene series which are substituted by hydroxyl in the phenyl orna hthyl nucleus. Such oxyphenylor oXynap thylpyrazolones were hithertn not employed practically for the manufacture of dyestufis to be chromated subsequently. The observation that they furnish with the diazo compounds derivated from the orthoaminonaphthols as well as with those derivated from the orthoaminophenols dyestufis which are prominent fast have been chromated, is therefore absolutely new and surprising. The said oxyphenylor oxynaphthylpyrazolones are obtained in the known manner by condensing the oxy derivates of phenylor naphthylhydrazin and their substitution products, prepared themselves from the corresponding diazophenols or diazonaphthols,

While the combination orthodiazo- Application filed December 31, 1915. Serial No. 69,652.

for instance, with acetylic acetic ester and producing subsequently the nucleus closing required for the formation of a pyrazolone derivate. The thus obtained dyestuffs derived from oxyphenylor oxynaphthylpyrazolones and orthodiazophenol derivates dye wool yellow to Bordeaux-red tints turning to orange to red by their subsequent treatment with chromium compounds, as for instance chromium salts or bichromates. The subsequently chromated dyeings possess an excellent fastness to fulling, potting and light, similar to that of the dyestufis derived from orthoaminonaphtholsulfonic acids and the hitherto employed pyrazolones. The new dyestuffs permit to produce on wool valuable. fast, orange to yellowish red chromated tints which could not be produced with the dyestufis hitherto subsequently chromated.

If instead of diazophenol derivates the diazooxids of, the naphthalene series are combined in an analogous manner with oxyphenylor oxynaphthylpyrazolones, bluishred dyestufi's are obtained which are still more fast to fulling and potting than those above specified, that is to say than the best hitherto known red dyestufis subsequently chromated.

Obviously the production of fast dyeings with the dyestuffs of the present application can be eflected, not by subsequent chromating, but also according to other processes employed for mordant-dyestuffs, as for instance by dyeing on chromium mordanted wool or by dyeing in a bath containing at least a solved chromate.

The new dyestuffs constitute in a dry state yellow to red powders, soluble in concentrated sulfuric acid with intense colorations and in water with yellow to red colorations.

Example-Dyestufi' from 0rthoamin0- phenolsulfonic acid and the pymzoione denon 18.9 parts orthoaminophenolsulfonic acid low solutions.

are diazotized in a known manner and joined to the soda alkaline solution of 23.5 parts 5-nitro-2-oxyphenylmethylpyrazolone. The immediately out, pressed and dried. It constitutes in a dry state a, yellow powderdissolving in water and concentrated sulfuric acid to yel- It dyes wool in an acid bath formed dystufl' is saltedyellow tints turning tdred -orange by a subsequent treatment with chromium. The sub- 10 .sequently chromated dyeings possess a Dyestuff resulting fromgg z fif Dyeing on wool.

Themethyl pyrazolone derived from And the diazo derivate of- Water. fi g g Directly. fi i gg xk Para-nitreortho-aminophenol. o-Amlnohenol-sulfomc acid Ortho-aminophenol-sul omcacld... o-Aminop ienolsulfonlc acid.....

Do pfNitro-oaminophenol Yellow Red.... ed-orange itroamino-p-cresol Orange-red Bordeaux. ed. Picramic acid Yellow Brown Brown. 1:2:4-Anfl11onap1thol-sulfonica Blue-red.... Orange Blue-red o-Aminopheno uliom'c acid Yellow BIue-red.... Yellow Red-orange p-Ammo-p-cresolsullonic acid.... Yellow Red range-yel- Bed.

w. o-Aminophenolsulfonic acid Yellow Yellow Yellow Red-orange. p-Nitro-o-amino henol Red Red-orange. O-AminO-p-creso sulfonic acid Red Oil-ange-yel- Red.

. ow. Nitroamino-p-cresol Red Red-brown. Red. phlgr-o-aminophenol-osulionic acid. Brown-red.. 0 Orange Red. icramic acid Orange Brown Red-brown. Do 1:2:4-Aminona htholsulfom acid Orange Orange Red. 2:5:7-Aminonaphtholsuliom cac d o-Aminopheno sultonic acid Orange. Orange Brown. 2:5:7-Aminonaphtholsulfomc 801d. p-Nitroo-aminophenol Red-bro Brown-red.. Brown.

Do :2z4-Aminonaphtholsulfonic acid. Orange.. Orange Blue-red. 4-Sullo-2-ammo-1-ph carboni acid Nitr0-0-amin0phenol Orange... Red-orange. Red-orange. itr0amino-pcresol............ Blue-red. Bordeaux... Yellow-red. Para-aminosalicylicacid p-chlor-o-ammophenol Yellow Orange Red.

What I claim is; I 1. The described process for the manufacture of orange to red dyestuffs ableto be chromated, consisting in combining an orthooxydiazo compound with a pyrazolone facture of orange to red dyestuffs able to be chromated, consisting in combining the diazo derivative of an orthoaminophenolor an orthoaminonaphthol compound with a pyrazolone derivate of the benzene or the naphthalene series substituted by hydroxyl in the phenylor naphthyl nucleus.

3. As new product's-the described orange to red. dyestuffs able to be chromated, which are derived from an orthooxydiazo compound and a pyrazolone derivate of the benzene or the naphthalene series substituted by by droxyl in the phenylor 'naphthyl nucleus and which constitute yellow to red powders soluble in concentrated sulfuric acid withintense colorations and in water to yellow to red solutions dyeing animal fibers according to the known processes used for chromium dyestuffs, orange to brown and red tints fast to fulling, potting and light. I

gned

In witness whereof I have hereunto si my name thisv second day of December, 1915,

in the presence of two subscrib DR. Witnesses:

ARNOLD ZUBER, ORMoNn RITTER.

ing witnesses. J AGERSPACHER.

dyestuffs prepared 15 

